[(2R,3S,4S,5R,6S)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

Details

• Internal ID: 93bafe32-a34d-470b-ad1f-088d960d3df0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate
• SMILES (Canonical): C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)COC(=O)C4=C(C(=CC=C4)O)O)O)O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=C(C(=CC=C4)O)O)O)O)O
• InChI: InChI=1S/C23H26O12/c1-2-10-11-6-7-31-21(30)13(11)8-33-22(10)35-23-19(28)18(27)17(26)15(34-23)9-32-20(29)12-4-3-5-14(24)16(12)25/h2-5,8,10-11,15,17-19,22-28H,1,6-7,9H2/t10-,11+,15-,17-,18+,19-,22+,23+/m1/s1
• InChI Key: JMJYZUZXYVEGII-UVPQXQFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₂
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.14242626 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.32
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4835	48.35%
Caco-2	-	0.8933	89.33%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	0.8490	84.90%
OATP1B1 inhibitior	+	0.8344	83.44%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9232	92.32%
P-glycoprotein inhibitior	-	0.6098	60.98%
P-glycoprotein substrate	-	0.6784	67.84%
CYP3A4 substrate	+	0.6613	66.13%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8912	89.12%
CYP2C9 inhibition	-	0.6155	61.55%
CYP2C19 inhibition	-	0.6221	62.21%
CYP2D6 inhibition	-	0.8383	83.83%
CYP1A2 inhibition	-	0.7217	72.17%
CYP2C8 inhibition	+	0.6941	69.41%
CYP inhibitory promiscuity	-	0.8067	80.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6534	65.34%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.8848	88.48%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6667	66.67%
Micronuclear	-	0.5667	56.67%
Hepatotoxicity	-	0.6466	64.66%
skin sensitisation	-	0.7544	75.44%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8007	80.07%
Acute Oral Toxicity (c)	III	0.4859	48.59%
Estrogen receptor binding	+	0.8489	84.89%
Androgen receptor binding	+	0.6580	65.80%
Thyroid receptor binding	+	0.5702	57.02%
Glucocorticoid receptor binding	+	0.6464	64.64%
Aromatase binding	+	0.6213	62.13%
PPAR gamma	+	0.7285	72.85%
Honey bee toxicity	-	0.8251	82.51%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9512	95.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	97.17%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.45%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.07%	95.17%
CHEMBL2581	P07339	Cathepsin D	92.71%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.47%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.39%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.29%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.62%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.33%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.70%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	85.75%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	85.63%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.23%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.15%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.66%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.00%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.50%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.79%	100.00%
CHEMBL3891	P07384	Calpain 1	80.46%	93.04%

Plants that contains it

• Gentiana algida

Cross-Links

• PubChem: 102094443
• LOTUS: LTS0153614
• wikiData: Q105131488